Bill De Blasio For NYC Mayor: Can The Public Advocate Go From Master Strategist To Mister Mayor?

The year: 1980. At stake: the presidency of NYU’s Weinstein Hall dorm.

“It was a hotly, hotly contested race,” Public Advocate Bill de Blasio recalls of his first campaign. His opponent was thwarting his visibility at every turn, ripping down Mr. de Blasio’s posters in the middle of the night.

A disgusted Mr. de Blasio and his team met for an emergency strategy session. “We decided the only thing to do was to have people awake at all hours to replace the posters immediately,” he explained to The Observer last week.

“Our opponents eventually just stopped because they knew they could not defeat our awesome outreach machinery,” he said with a grin. “It was an early lesson in persistence.”

In his all-but-certain mayoral bid, Mr. de Blasio will need equally awesome outreach machinery and at least as much persistence. Even though campaign season doesn’t officially kick off until next year, he currently polls a distant third, in a race fronted by Council Speaker Christine Quinn, with her dominating approval ratings, brimming war chest, and the history-making appeal of potentially being the city’s first female and first openly gay mayor. (Former Comptroller William Thompson typically polls in second place, ahead of Mr. de Blasio and fourth-place contender John Liu, the city’s current comptroller.)

This time around, poster saboteurs will be the least of Mr. de Blasio’s worries as he to attempts to stand out for more than his 6-foot-5 stature. “It’s healthy, it’s healthy,” Mr. de Blasio countered when we brought up his lack of name recognition. “I can tell when I get on the subway, I can tell when I go to the grocery store—it’s evolving all the time.”

In many ways, the mayoral race is a perfect next step for Mr. de Blasio, 51, a savvy tactician who has ascended to a series of local offices using the same political acumen that he deployed in his previous career as a campaign operative for former Mayor David Dinkins, former Senator Hillary Clinton and others.

Mr. de Blasio possesses “real strategic sense and smarts about politics,” said Harold Ickes, a former top aide to President Clinton who picked Mr. de Blasio to manage Ms. Clinton’s 2000 Senate campaign. Mr. Ickes and others recalled how her operation struggled at first, and they credited Mr. de Blasio with turning things around. “Bill’s determination, his personality and values—and not taking himself all that seriously and a sense of humor—won the support of many, many people on the inside,” Mr. Ickes said.

As public advocate, an office he has held since 2010, Mr. de Blasio has found his niche trying to be the chief progressive antagonist to Mayor Michael Bloomberg’s administration. He railed against some of the mayor’s school closures, against the city’s widening economic gap, against the NYPD’s controversial stop-and-frisk tactic, and on down the list. Whenever there is space to Mr. Bloomberg’s left in the public discussion, Mr. de Blasio can be found there, usually holding a press conference.

This has occasionally frustrated Mr. Bloomberg. “He wants to drive everybody out of the city, but that’s okay,” the mayor scoffed, after Mr. de Blasio proposed a tax-the-rich idea in mid-October.

One of Mr. Bloomberg’s top aides, Deputy Mayor Howard Wolfson, characterized Mr. de Blasio as an opportunist. “I think Bill’s made a political calculation that being the antagonist to Bloomberg in the race is his best positioning,” he told The Observer. “He’s been in politics for a very long time as an operative, so I know that he would have thought about that pretty hard.”

Mr. Wolfson, who worked closely with Mr. de Blasio on Ms. Clinton’s senatorial bid, pointed to Mr. Bloomberg’s strong approval rating among Democrats in a Quinnipiac University poll taken in the wake of Hurricane Sandy. Although 55 percent of Republicans disapproved of the mayor, possibly rankled by his in-your-face public-health initiatives, 61 percent of Democrats actually approved.

“I think [Mr. de Blasio] has come to the conclusion that unless you’re criticizing the mayor, you’re not getting a lot of press,” Mr. Wolfson said. “I think he’s made that decision of how to get a lot of oxygen, but I think, ultimately, throwing bricks at the guy who’s at 60 percent among Democrats is not a winning strategy.”

FOLLOWING A DORM presidency advocating for improved student life and lower tuition, Mr. de Blasio graduated to a series of jobs in nonprofit groups. He landed on David Dinkins’s mayoral campaign in 1989, as a volunteer coordinator. “I was literally the lowest person on the totem pole. If you go and find the old organizational chart, I was the lowest ranking, lowest paid,” he recalled.

When Mr. Dinkins won, Mr. de Blasio secured a job as a City Hall aide, a four-year position “foundational for everything I’ve done since then,” he said. Not only did Mr. de Blasio acquire a taste for politics, he made a series of instrumental contacts, including another young Dinkins aide named Chirlane McCray, whom he met in 1991 and eventually married.

It was the birth of their first child in 1994 that first gave Mr. de Blasio the idea of running for office on his own, in a roundabout sort of way. It was right after Mr. Dinkins’s loss to Rudy Giuliani, and Mr. de Blasio found himself job-hunting again.

“I had gotten used to the fact that the long-term path I had been on had been fundamentally interrupted, and I was trying to make sense of where to go next,” he remembered. “When you’re about to have a baby, they do this little survey about your conditions at home and one thing and another. The social worker at Methodist Hospital asked about Chirlane, where she worked, one thing and another; then she asked about me, and I said, ‘I’m currently unemployed.’ She started furiously scribbling. I was like, ‘No, wait! It happens a lot in my trade!’”

It would be seven years and even more campaigns before Mr. de Blasio struck out on his own, leaping into a local City Council race in Park Slope. The incumbent councilman had been term-limited out of office, and a crowded field of aspiring politicians emerged to replace him. But with powerful fund-raising connections left over from his operative days, a biography that included work on the local school board and an aggressive door-knocking operation, Mr. de Blasio was able to notch the victory.

Once elected, he put his political mind to work again, climbing the ranks of the City Council and even making an unsuccessful attempt at the speakership in 2005. But by sticking to the progressive topics core to the Democratic electorate, he positioned himself to run for higher office, and in 2009, he set his sights on outgoing Public Advocate Betsy Gotbaum’s job. “It seemed like a natural fit on many levels,” Mr. de Blasio said of the decision, adding that the issues of child welfare and poverty that he worked on while on the Council “clearly fit the purview of the Public Advocate’s Office.”

But it was a hard-fought race for Mr. de Blasio. “He ran against very, very well-qualified opponents,” recalled Ken Sunshine, Mr. de Blasio’s former boss in the Dinkins administration. The field included not only another prominent councilman, but also Mark Green, a former public advocate who characterized the race as “a contest between an effective consumer advocate and a lifelong political insider.” Although Mr. Green led in the public polling, Mr. de Blasio managed to edge him out with a labor-backed coalition that could forage for votes on every block. As Mr. Sunshine phrased it, “Basically, Bill kicked his ass.”

Political insider or not, Mr. de Blasio has gone out of his way to solidify his liberal credentials, regardless of the audience. For example, he presented his plan to tax the city’s wealthiest residents at a Conrad Hotel ballroom filled with, well, some of the city’s wealthiest residents. “Now, some of you may be thinking that this is an interesting place to come and make this proposal,” Mr. de Blasio mused. “You might say, ‘You have come to the lion’s den.’” He pivoted: “Well, I think it’s a room full of people who care about New York City.”

Just last week, Mr. de Blasio threw himself to the so-called lions again at a pro-business forum hosted by Crain’s New York Business at the Sheraton, using the very first question to tout his tax proposal.

The plan, which would generate $532 million per year in revenue from those making $500,000 or more, has become a key part of Mr. de Blasio’s agenda. And the program the tax hike would fund? Why, it would be for universal early education, which happens to be a top priority of Mr. de Blasio’s top opponent for next year, City Council Speaker Christine Quinn.

Education is hardly the sole issue on which Mr. de Blasio has sought to outflank Ms. Quinn. Before Sandy blew away politics as usual, Mr. de Blasio could be found spending his Sundays at African-American churches in Central Brooklyn and southeastern Queens, harping on Ms. Quinn for blocking paid sick day legislation in her chamber.

At a mid-October appearance at a Bed-Stuy church, Mr. de Blasio took swipes at both Mr. Bloomberg and Ms. Quinn for their stance on paid sick days. “The mayor—this may shock you—the mayor doesn’t think we need paid sick leave days. Apparently, for him, it’s not something he feels he needs. Maybe the same people he hangs out with don’t feel they need it. But over a million New Yorkers do. We have to tell the mayor, we have to tell the City Council, we especially have to tell Speaker Quinn in the City Council, who will not bring this to a vote: ‘It’s time to bring this to a vote.’”

Mr. de Blasio, whose wife is African-American and an unpaid adviser to his campaign, even attempted some corny church-related humor that the crowd actually seemed to appreciate.

“As a public servant, it would only be my obligation to report a situation like this, because I would have to call the fire department, because the choir is on fire!” he joked to open his speech. “But maybe it’s not necessary to call the fire department, because of the cool, smooth stylings of the band!”

While he naturally hopes to make inroads with black voters, his campaign plan, as multiple aides described it, is aggressively focused on the outer boroughs, which are home to 80 percent of the city’s population but have produced very few of the city’s mayors.

MR. DE BLASIO, who grew up in Massachusetts, lives in a cheerful but modest yellow South Slope row house with weathered vinyl siding and his Ford Escape hybrid only occasionally parked out front. His daughter Chiara graduated Beacon High School last year and now attends college; his son, Dante, is a high school sophomore at Brooklyn Tech.

“He’s not like a packaged product,” said Mr. Sunshine, a longtime friend of Mr. de Blasio’s. He then paused for a faux-cough that sounded an awful lot like “Mitt Romney,” adding, “He’s very normal, which is maybe the most unique quality of someone who wants to be mayor of New York.”

As evidence of his own normalcy, Mr. de Blasio points to his decision to send his children to New York City public schools. As do his aides, repeatedly. Apparently, kids in public schools amount to a political advantage none of the city’s other recent mayors—nor Ms. Quinn—can claim. “Being a public school parent is a big fucking deal,” Mr. Sunshine explained.

Additionally, besides casting Ms. Quinn as too conservative on economic issues, both Mr. de Blasio and his supporters constantly reference the Quinn-backed 2009 term-limits extension, hoping it will come back to haunt her, four more Bloomberg years later.

While it’s still early in a likely fluid race, according to the public polls, Mr. de Blasio certainly has his work cut out for him. The latest survey gave Ms. Quinn a 65 percent approval rating among Democrats and a solid lead overall, with 32 percent of the total vote. Mr. de Blasio, with 49 percent approval, stood at 9 percent of the total vote. Whether Mr. de Blasio can maneuver his way into anything even close to a lead remains to be seen.

“I think as a political operative he’s had a very long track record of success,” Mr. Wolfson said. “Whether being a political operative is the right background for being a mayor and a chief executive is, in my opinion, a different issue.”

FOLLOWING A DORM presidency advocating for improved student life and lower tuition, Mr. de Blasio graduated to a series of jobs in nonprofit groups. He landed on David Dinkins’s mayoral campaign in 1989, as a volunteer coordinator. “I was literally the lowest person on the totem pole. If you go and find the old organizational chart, I was the lowest ranking, lowest paid,” he recalled.

When Mr. Dinkins won, Mr. de Blasio secured a job as a City Hall aide, a four-year position “foundational for everything I’ve done since then,” he said. Not only did Mr. de Blasio acquire a taste for politics, he made a series of instrumental contacts, including another young Dinkins aide named Chirlane McCray, whom he met in 1991 and eventually married.

It was the birth of their first child in 1994 that first gave Mr. de Blasio the idea of running for office on his own, in a roundabout sort of way. It was right after Mr. Dinkins’s loss to Rudy Giuliani, and Mr. de Blasio found himself job-hunting again.

“I had gotten used to the fact that the long-term path I had been on had been fundamentally interrupted, and I was trying to make sense of where to go next,” he remembered. “When you’re about to have a baby, they do this little survey about your conditions at home and one thing and another. The social worker at Methodist Hospital asked about Chirlane, where she worked, one thing and another; then she asked about me, and I said, ‘I’m currently unemployed.’ She started furiously scribbling. I was like, ‘No, wait! It happens a lot in my trade!’”

It would be seven years and even more campaigns before Mr. de Blasio struck out on his own, leaping into a local City Council race in Park Slope. The incumbent councilman had been term-limited out of office, and a crowded field of aspiring politicians emerged to replace him. But with powerful fund-raising connections left over from his operative days, a biography that included work on the local school board and an aggressive door-knocking operation, Mr. de Blasio was able to notch the victory.

Once elected, he put his political mind to work again, climbing the ranks of the City Council and even making an unsuccessful attempt at the speakership in 2005. But by sticking to the progressive topics core to the Democratic electorate, he positioned himself to run for higher office, and in 2009, he set his sights on outgoing Public Advocate Betsy Gotbaum’s job. “It seemed like a natural fit on many levels,” Mr. de Blasio said of the decision, adding that the issues of child welfare and poverty that he worked on while on the Council “clearly fit the purview of the Public Advocate’s Office.”

But it was a hard-fought race for Mr. de Blasio. “He ran against very, very well-qualified opponents,” recalled Ken Sunshine, Mr. de Blasio’s former boss in the Dinkins administration. The field included not only another prominent councilman, but also Mark Green, a former public advocate who characterized the race as “a contest between an effective consumer advocate and a lifelong political insider.” Although Mr. Green led in the public polling, Mr. de Blasio managed to edge him out with a labor-backed coalition that could forage for votes on every block. As Mr. Sunshine phrased it, “Basically, Bill kicked his ass.”

Political insider or not, Mr. de Blasio has gone out of his way to solidify his liberal credentials, regardless of the audience. For example, he presented his plan to tax the city’s wealthiest residents at a Conrad Hotel ballroom filled with, well, some of the city’s wealthiest residents. “Now, some of you may be thinking that this is an interesting place to come and make this proposal,” Mr. de Blasio mused. “You might say, ‘You have come to the lion’s den.’” He pivoted: “Well, I think it’s a room full of people who care about New York City.”

Just last week, Mr. de Blasio threw himself to the so-called lions again at a pro-business forum hosted by Crain’s New York Business at the Sheraton, using the very first question to tout his tax proposal.

The plan, which would generate $532 million per year in revenue from those making $500,000 or more, has become a key part of Mr. de Blasio’s agenda. And the program the tax hike would fund? Why, it would be for universal early education, which happens to be a top priority of Mr. de Blasio’s top opponent for next year, City Council Speaker Christine Quinn.

Education is hardly the sole issue on which Mr. de Blasio has sought to outflank Ms. Quinn. Before Sandy blew away politics as usual, Mr. de Blasio could be found spending his Sundays at African-American churches in Central Brooklyn and southeastern Queens, harping on Ms. Quinn for blocking paid sick day legislation in her chamber.

At a mid-October appearance at a Bed-Stuy church, Mr. de Blasio took swipes at both Mr. Bloomberg and Ms. Quinn for their stance on paid sick days. “The mayor—this may shock you—the mayor doesn’t think we need paid sick leave days. Apparently, for him, it’s not something he feels he needs. Maybe the same people he hangs out with don’t feel they need it. But over a million New Yorkers do. We have to tell the mayor, we have to tell the City Council, we especially have to tell Speaker Quinn in the City Council, who will not bring this to a vote: ‘It’s time to bring this to a vote.’”

Mr. de Blasio, whose wife is African-American and an unpaid adviser to his campaign, even attempted some corny church-related humor that the crowd actually seemed to appreciate.

“As a public servant, it would only be my obligation to report a situation like this, because I would have to call the fire department, because the choir is on fire!” he joked to open his speech. “But maybe it’s not necessary to call the fire department, because of the cool, smooth stylings of the band!”

While he naturally hopes to make inroads with black voters, his campaign plan, as multiple aides described it, is aggressively focused on the outer boroughs, which are home to 80 percent of the city’s population but have produced very few of the city’s mayors.

MR. DE BLASIO, who grew up in Massachusetts, lives in a cheerful but modest yellow South Slope row house with weathered vinyl siding and his Ford Escape hybrid only occasionally parked out front. His daughter Chiara graduated Beacon High School last year and now attends college; his son, Dante, is a high school sophomore at Brooklyn Tech.

“He’s not like a packaged product,” said Mr. Sunshine, a longtime friend of Mr. de Blasio’s. He then paused for a faux-cough that sounded an awful lot like “Mitt Romney,” adding, “He’s very normal, which is maybe the most unique quality of someone who wants to be mayor of New York.”

As evidence of his own normalcy, Mr. de Blasio points to his decision to send his children to New York City public schools. As do his aides, repeatedly. Apparently, kids in public schools amount to a political advantage none of the city’s other recent mayors—nor Ms. Quinn—can claim. “Being a public school parent is a big fucking deal,” Mr. Sunshine explained.

Additionally, besides casting Ms. Quinn as too conservative on economic issues, both Mr. de Blasio and his supporters constantly reference the Quinn-backed 2009 term-limits extension, hoping it will come back to haunt her, four more Bloomberg years later.

While it’s still early in a likely fluid race, according to the public polls, Mr. de Blasio certainly has his work cut out for him. The latest survey gave Ms. Quinn a 65 percent approval rating among Democrats and a solid lead overall, with 32 percent of the total vote. Mr. de Blasio, with 49 percent approval, stood at 9 percent of the total vote. Whether Mr. de Blasio can maneuver his way into anything even close to a lead remains to be seen.

“I think as a political operative he’s had a very long track record of success,” Mr. Wolfson said. “Whether being a political operative is the right background for being a mayor and a chief executive is, in my opinion, a different issue.”